SCOPUS 정보 검색 플랫폼

Volumn 2007, Issue 12, 2007, Pages 132-147

Synthesis of triazolopyridines and triazolopyrimidines using a modified Mitsunobu reaction

(7) Roberge, Jacques Y a Yu, Guixue a Mikkilineni, Amarendra a Wu, Ximao a Zhu, Yeheng a Lawrence, R Michael a Ewing, William R a

a BRISTOL MYERS SQUIBB RESEARCH AND DEVELOPMENT (United States)

Author keywords

Intramolecular cyclization; Mitsunobu reaction; Triazolopyridines; Triazolopyrimidines

Indexed keywords

EID: 34250334344 PISSN: 1551-7012 EISSN: 14246376 Source Type: Journal
DOI: 10.3998/ark.5550190.0008.c10 Document Type: Article

Times cited : (17)

References (39)

1
- 0035829179
- (a) Lawson, E. C.; Hoekstra, W. J.; Addo, M. F.; Andrade-Gordon, P.; Damiano, B. P.; Kauffman, J. A.; Mitchell, J. A.; Maryanoff, B. E. Bioorg. Med. Chem. Lett. 2001, 11, 2619.
- (2001) Bioorg. Med. Chem. Lett , vol.11 , pp. 2619
- Lawson, E.C.¹ Hoekstra, W.J.² Addo, M.F.³ Andrade-Gordon, P.⁴ Damiano, B.P.⁵ Kauffman, J.A.⁶ Mitchell, J.A.⁷ Maryanoff, B.E.⁸

2
- 0345269287
- 1229.1229
- (b) Baraldi, P. G.; Fruttarolo, F.; Tabrizi, M. A.; Preti, D.; Romagnoli, R.; El-Kashef, H.; Moorman, A.; Varani, K.; Gessi, S.; Merighi, S.; Borea, P. A. J. Med. Chem. 2003, 46, 1229.1229.
- (2003) J. Med. Chem , vol.46
- Baraldi, P.G.¹ Fruttarolo, F.² Tabrizi, M.A.³ Preti, D.⁴ Romagnoli, R.⁵ El-Kashef, H.⁶ Moorman, A.⁷ Varani, K.⁸ Gessi, S.⁹ Merighi, S.¹⁰ Borea, P.A.¹¹

3
- 0030856515
- (c) Livi, O.; Scartoni, V. Farmaco 1997, 52, 205.
- (1997) Farmaco , vol.52 , pp. 205
- Livi, O.¹ Scartoni, V.²

4
- 0025152999
- (d) Roberts, D. A.; Bradbury, R. H.; Brown, D.; Faull, A.; Griffiths, D.; Major, J. S.; Oldham, A. A.; Pearce, R. J.; Ratcliffe, A. H.; Revill, J.; Waterson, D. J. Med. Chem. 1990, 33, 2326.
- (1990) J. Med. Chem , vol.33 , pp. 2326
- Roberts, D.A.¹ Bradbury, R.H.² Brown, D.³ Faull, A.⁴ Griffiths, D.⁵ Major, J.S.⁶ Oldham, A.A.⁷ Pearce, R.J.⁸ Ratcliffe, A.H.⁹ Revill, J.¹⁰ Waterson, D.¹¹

5
- 33745699202
- (e) McClure, K. F.; Letavic, M. A.; Kalgutkar, A. S.; Gabel, C. A.; Audoly, L.; Barberia, J. T.; Braganza, J. F.; Carter, D.; Carty, T. J.; Cortina, S. R., Bioorg. Med. Chem. Lett. 2006, 16, 4339.
- (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 4339
- McClure, K.F.¹ Letavic, M.A.² Kalgutkar, A.S.³ Gabel, C.A.⁴ Audoly, L.⁵ Barberia, J.T.⁶ Braganza, J.F.⁷ Carter, D.⁸ Carty, T.J.⁹ Cortina, S.R.¹⁰

6
- 0008330703
- (a) Jones, G.; Sliskovic, D. R. Adv. Heterocyclic Chem. 1983, 34, 79.
- (1983) Adv. Heterocyclic Chem , vol.34 , pp. 79
- Jones, G.¹ Sliskovic, D.R.²

7
- 0000181858
- (b) Zhang, Z.-Y.; Sun, X.-W. Heterocycles 1998, 48, 561.
- (1998) Heterocycles , vol.48 , pp. 561
- Zhang, Z.-Y.¹ Sun, X.-W.²

8
- 0034641008
- (c) Lawson, E. C.; Maryanoff, B. E.; Hoekstra, W. J. Tetrahedron Lett. 2000, 41, 4533.
- (2000) Tetrahedron Lett , vol.41 , pp. 4533
- Lawson, E.C.¹ Maryanoff, B.E.² Hoekstra, W.J.³

9
- 84987285046
- (d) Schneller, S. W.; Bartholomew, D. G. J. Heterocycl. Chem. 1978, 15, 439.
- (1978) J. Heterocycl. Chem , vol.15 , pp. 439
- Schneller, S.W.¹ Bartholomew, D.G.²

10
- 0013006166
- (e) Shaban, M. A. E.; Morgan, A. E. A. Adv. Heterocyclic Chem. 2000, 77, 345.
- (2000) Adv. Heterocyclic Chem , vol.77 , pp. 345
- Shaban, M.A.E.¹ Morgan, A.E.A.²

11
- 33947334632
- (f) Potts, K. T.; Burton, H. R. J Org Chem. 1966, 31, 251.
- (1966) J Org Chem , vol.31 , pp. 251
- Potts, K.T.¹ Burton, H.R.²

12
- 0001527066
- (g) Potts, K. T., Burton, H. R.; Roy, S. K. J. Org. Chem. 1966, 31, 265.
- (1966) J. Org. Chem , vol.31 , pp. 265
- Potts, K.T.¹ Burton, H.R.² Roy, S.K.³

13
- 33947338253
- (h) Potts, K.T.; Burton, H.R.; Crawford; T.H.; Thomas, S.W. J. Org. Chem. 1966, 31, 3522.
- (1966) J. Org. Chem , vol.31 , pp. 3522
- Potts, K.T.¹ Burton, H.R.² Crawford, T.H.³ Thomas, S.W.⁴

14
- 85082966655
- (a) Wamhoff, H.; Zahran, M. Synthesis, 1987, 876.
- (1987) Synthesis , pp. 876
- Wamhoff, H.¹ Zahran, M.²

15
- 0034728125
- (b) Collins, I.; Castro, J. L.; Street, L. J. Tetrahedron Lett. 2000, 41, 781.
- (2000) Tetrahedron Lett , vol.41 , pp. 781
- Collins, I.¹ Castro, J.L.² Street, L.J.³

16
- 20144388228
- (c) Kim, D.; Wang, L.; Hale, J. J.; Lynch, C. L.; Budhu, R. J.; MacCoss, M.; Mills, S. G.; Malkowitz, L.; Gould, S. L.; DeMartino, J. A. Bioorg. Med. Chem. Lett. 2005, 15, 2129.
- (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 2129
- Kim, D.¹ Wang, L.² Hale, J.J.³ Lynch, C.L.⁴ Budhu, R.J.⁵ MacCoss, M.⁶ Mills, S.G.⁷ Malkowitz, L.⁸ Gould, S.L.⁹ DeMartino, J.A.¹⁰

17
- 33748901833
- (d) Moulin, A.; Martinez, J.; Fehrentz, J.-A. Tetrahedron Lett. 2006, 47, 7591.
- (2006) Tetrahedron Lett , vol.47 , pp. 7591
- Moulin, A.¹ Martinez, J.² Fehrentz, J.-A.³

18
- 0001633349
- (a) Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380.
- (1967) Bull. Chem. Soc. Jpn , vol.40 , pp. 2380
- Mitsunobu, O.¹ Yamada, M.²

19
- 0001033833
- (b) Mitsunobu, O.; Yamada; M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1967, 40, 935.
- (1967) Bull. Chem. Soc. Jpn , vol.40 , pp. 935
- Mitsunobu, O.¹ Yamada, M.² Mukaiyama, T.³

20
- 0037231022
- (c) Valentine, D. H., Jr.; Hillhouse, J. H. Synthesis 2003, 317.
- (2003) Synthesis , pp. 317
- Valentine Jr., D.H.¹ Hillhouse, J.H.²

21
- 0001640928
- (d) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127.
- (1996) Org. Prep. Proc. Int , vol.28 , pp. 127
- Hughes, D.L.¹

22
- 0028840084
- (a) De Lombaert, S.; Blanchard, L.; Tan, J.; Sakane, Y.; Berry, C.; Ghai, R. D. Bioorg. Med. Chem. Lett. 1995, 5, 145.
- (1995) Bioorg. Med. Chem. Lett , vol.5 , pp. 145
- De Lombaert, S.¹ Blanchard, L.² Tan, J.³ Sakane, Y.⁴ Berry, C.⁵ Ghai, R.D.⁶

23
- 0001250488
- (b) Duncia, J. V.; Pierce, M. E.; Santella, J. B. III. J. Org. Chem. 1991, 56, 2395.
- (1991) J. Org. Chem , vol.56 , pp. 2395
- Duncia, J.V.¹ Pierce, M.E.² Santella III, J.B.³

24
- 0036428125
- (a) Dallinger, D.; Kappe, C. O. Synlett 2002, 11, 1901.
- (2002) Synlett , vol.11 , pp. 1901
- Dallinger, D.¹ Kappe, C.O.²

25
- 0003850608
- Pearson, A. J, Roush, W. R. J. Eds; Wiley and Son: New York
- (b) Jenkins, I. D.; Mitsunobu, O. in Handbook of Reagents for Organic Synthesis; Pearson, A. J.; Roush, W. R. J. Eds; Wiley and Son: New York, 1999; p 459.
- (1999) Handbook of Reagents for Organic Synthesis , pp. 459
- Jenkins, I.D.¹ Mitsunobu, O.²

26
- 0030865756
- Wang, F.; Hauske, J. R. Tetrahedron Lett. 1997, 38, 6529.
- (1997) Tetrahedron Lett , vol.38 , pp. 6529
- Wang, F.¹ Hauske, J.R.²

27
- 0035006416
- Other phosphine based amide dehydration reagents have been reported: (a) Sugimoto, O.; Mori, M.; Moriya, K.; Tanji, K.-i. Helv. Chim. Acta 2001, 84, 1112.
- Other phosphine based amide dehydration reagents have been reported: (a) Sugimoto, O.; Mori, M.; Moriya, K.; Tanji, K.-i. Helv. Chim. Acta 2001, 84, 1112.

28
- 1642528348
- (b) Zhong, Y.-L.; Lee, J.; Reamer, R. A.; Askin, D. Org. Lett. 2004, 6, 929.
- (2004) Org. Lett , vol.6 , pp. 929
- Zhong, Y.-L.¹ Lee, J.² Reamer, R.A.³ Askin, D.⁴

29
- 0009554450
- Konnecke, A.; Dorre, R.; Lippmann, E. Tetrahedron Lett. 1978, 19, 2071.
- (1978) Tetrahedron Lett , vol.19 , pp. 2071
- Konnecke, A.¹ Dorre, R.² Lippmann, E.³

30
- 0033529819
- Similar conditions have been used for azidation of 1,2- and 1,3-diols. See: He, L.; Wanunu, M.; Byun, H.-S.; Bittman, R. J. Org. Chem. 1999, 64, 6049.
- Similar conditions have been used for azidation of 1,2- and 1,3-diols. See: He, L.; Wanunu, M.; Byun, H.-S.; Bittman, R. J. Org. Chem. 1999, 64, 6049.

31
- 0028041388
- It has been proposed that when using HN3 in the Mitsunobu reaction, the azide may add to the phosphonium ylide intermediate and increase its reactivity. See: Afonso, C. M, Barros, M. T, Godinho, L. S, Maycock, C. D. Tetrahedron 1994, 50, 9671
- It has been proposed that when using HN3 in the Mitsunobu reaction, the azide may add to the phosphonium ylide intermediate and increase its reactivity. See: Afonso, C. M.; Barros, M. T.; Godinho, L. S.; Maycock, C. D. Tetrahedron 1994, 50, 9671.

32
- 0000564744
- (a) Varasi, M.; Walker, K. A. M.; Maddox, M. L. J. Org. Chem. 1987, 52, 4235.
- (1987) J. Org. Chem , vol.52 , pp. 4235
- Varasi, M.¹ Walker, K.A.M.² Maddox, M.L.³

33
- 24744456324
- (b) Schenk, S.; Weston, J.; Anders, E. J. Am. Chem. Soc. 2005, 127, 12566.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 12566
- Schenk, S.¹ Weston, J.² Anders, E.³

34
- 84989531500
- 3P/DIAD has been used for azidation of alcohol see Viaud, M. C.; Rollin, P. Synthesis 1990, 130.
- 3P/DIAD has been used for azidation of alcohol see Viaud, M. C.; Rollin, P. Synthesis 1990, 130.

35
- 0000595912
- A referee pointed out the following reference: Volante, R. P. Tetrahedron Lett. 1981, 22, 3119 where the formation of a precipitate was observed within 30 min upon adding DIAD to Ph3P at a concentration of 0.4 M in THF at 0 °C. They reported that this precipitate was essential for the success of this reaction. In our case, we observed the formation of the precipitate only in the presence of TMS-N 3 at room temperature and a concentration of 0.1 M and as low as 0.05 M. When the substrate is present, the precipitate is often not observed or is seen only transiently. It is possible that we observed the formation of the same species as Volante and that the role of the TMS-N3 is to speed the formation of this intermediate but the fact that we do see an azide band in the IR of the solid suggest that we have a different species
- 3 is to speed the formation of this intermediate but the fact that we do see an azide band in the IR of the solid suggest that we have a different species.

36
- 85069239309
- 2 or from hexanes to ethyl acetate).
- 2 or from hexanes to ethyl acetate).

37
- 85069240019
- 2 (6 mL) and the white solid was filtered and dried under vacuum to give 317 mg of white solid (50% yield).
- 2 (6 mL) and the white solid was filtered and dried under vacuum to give 317 mg of white solid (50% yield).

38
- 15444367170
- Valeur, E.; Bradley, M. Chem. Comm. 2005, 1164.
- (2005) Chem. Comm , pp. 1164
- Valeur, E.¹ Bradley, M.²

39
- 24944516351
- McClure, K. F.; Abramov, Y. A.; Laird, E. R.; Barberia, J. T.; Cai, W.; Carty, T. J.; Cortina, S. R.; Danley, D. E.; Dipesa, A. J.; Donahue, K. M.; Dombroski, M. A.; Elliott, N. C.; Gabel, C. A.; Han, S.; Hynes, T. R.; LeMotte, P. K.; Mansour, M. N.; Marr, E. S.; Letavic, M. A.; Pandit, J.; Ripin, D. B.; Sweeney, F. J.; Tan, D.; Tao, Y., J. Med. Chem. 2005, 48, 5728.
- (2005) J. Med. Chem , vol.48 , pp. 5728
- McClure, K.F.¹ Abramov, Y.A.² Laird, E.R.³ Barberia, J.T.⁴ Cai, W.⁵ Carty, T.J.⁶ Cortina, S.R.⁷ Danley, D.E.⁸ Dipesa, A.J.⁹ Donahue, K.M.¹⁰ Dombroski, M.A.¹¹ Elliott, N.C.¹² Gabel, C.A.¹³ Han, S.¹⁴ Hynes, T.R.¹⁵ LeMotte, P.K.¹⁶ Mansour, M.N.¹⁷ Marr, E.S.¹⁸ Letavic, M.A.¹⁹ Pandit, J.²⁰ more..

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.